I now fly a 1947 35 Bonanza that my father owned for many years. My mother didn’t like to fly in small planes so when they traveled, my father flew the Bonanza and my mother would fly commercially. They arrived at this expensive but satisfactory arrangement after many years of disagreeing about how they should travel while on vacation.
One of my favorite family stories happened when my parents were both enroute to Florida. My father recognized the flight number for my mother’s airline flight on the VHF radio. With no objection from ATC, he talked air-to-air to the airliner and asked if they would let one of their passengers know that he was running a few minutes late.